Homestead Inn B&B

Nestled in Connecticut’s picturesque Housatonic Valley, the quaint town of New Milford—“where New England begins”—is home to the Homestead Inn, welcoming guests since 1928. Ideally located to enjoy all the area has to offer, including beloved community events like the Gilmore Girls Fan Fest, the Inn is the perfect place to stay.

The Homestead Inn features 16 well-appointed rooms across the Main House and Treadwell Annex, offering comfort and charm for every type of traveler. Whether you’re planning a romantic weekend getaway, a quick overnight stay, or corporate travel, the Inn provides a warm and inviting retreat.

Originally built around 1850 as a residence by John Prime Treadwell, the property became an inn in 1933, with the dining room added in 1940. Over the years, it has welcomed notable guests including the Joseph Kennedy family, conductor Leopold Stokowski, artist Philip Kappel, and actress Marilyn Monroe.

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